Latest deals
Insights
FAQs
Reviews
Price Alerts

Cheap flights from Wisconsin to Caribbean Islands from $106

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Wisconsin to Caribbean Islands departing on 12/1. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Wisconsin to Caribbean Islands

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
3:26 pm - 12:32 pmORD-SJU
19h 06m1 stop
Multiple Airlines Logo
1:59 am - 2:03 pmSJU-ORD
14h 04m1 stop
$210Multiple Airlines
Find Deal
Wed, Dec 10 - Sun, Dec 14
Multiple Airlines Logo
12:09 pm - 12:16 amORD-SJU
10h 07m1 stop
Multiple Airlines Logo
1:59 am - 2:03 pmSJU-ORD
14h 04m1 stop
$211Multiple Airlines
Find Deal
Wed, Dec 10 - Sun, Dec 14
Spirit Airlines Logo
11:40 am - 9:50 pmORD-SJU
8h 10m1 stop
Spirit Airlines Logo
8:45 pm - 11:59 pmSJU-ORD
5h 14mnonstop
$215Spirit Airlines
Find Deal
Mon, Nov 24 - Fri, Dec 5
Frontier Logo
6:11 pm - 10:17 amORD-SJU
14h 06m1 stop
Frontier Logo
2:29 am - 2:13 pmSJU-ORD
13h 44m1 stop
$216Frontier
Find Deal
Sat, Jan 10 - Sat, Jan 17
Spirit Airlines Logo
8:41 am - 3:17 pmORD-SJU
4h 36mnonstop
Spirit Airlines Logo
8:45 pm - 11:59 pmSJU-ORD
5h 14mnonstop
$217Spirit Airlines
Find Deal
Wed, Dec 3 - Mon, Dec 15
United Airlines Logo
2:20 pm - 9:00 pmORD-SJU
4h 40mnonstop
United Airlines Logo
4:52 pm - 8:20 pmSJU-ORD
5h 28mnonstop
$218United Airlines
Find Deal
Mon, Jan 19 - Fri, Jan 23
Frontier Logo
7:51 pm - 4:55 pmORD-SJU
19h 04m2 stops
Frontier Logo
4:11 pm - 11:35 pmSJU-ORD
9h 24m1 stop
$220Frontier
Find Deal
Sun, Jan 18 - Fri, Jan 30
Delta Logo
11:18 am - 11:44 pmORD-SJU
10h 26m1 stop
Delta Logo
6:27 pm - 11:57 pmSJU-ORD
7h 30m1 stop
$227Delta
Find Deal
Mon, Jan 19 - Tue, Jan 27
United Airlines Logo
6:00 am - 5:25 pmORD-PUJ
9h 25m1 stop
United Airlines Logo
2:55 pm - 6:08 pmPUJ-ORD
5h 13mnonstop
$293United Airlines
Find Deal
Mon, Dec 8 - Mon, Dec 15
Delta Logo
5:20 pm - 1:30 pmORD-PUJ
18h 10m1 stop
Delta Logo
2:32 pm - 9:42 pmPUJ-ORD
9h 10m1 stop
$342Delta
Find Deal
Sun, Jan 25 - Thu, Feb 5

Delta flights from Wisconsin to Caribbean Islands

Our best Delta deals on Wisconsin to Caribbean Islands flight tickets
Delta
Jan 19
ORD11:18 amChicago O'Hare Intl
10h 26m
1 stop
SJU11:44 pmSan Juan Luis Munoz Marin Intl
Jan 27
SJU6:27 pmSan Juan Luis Munoz Marin Intl
7h 30m
1 stop
ORD11:57 pmChicago O'Hare Intl
$227
Find similar
Delta
Jan 25
ORD5:20 pmChicago O'Hare Intl
18h 10m
1 stop
PUJ1:30 pmPunta Cana
Feb 5
PUJ2:32 pmPunta Cana
9h 10m
1 stop
ORD9:42 pmChicago O'Hare Intl
$342
Find similar
Delta
Dec 15
ORD5:07 pmChicago O'Hare Intl
18h 48m
2 stops
AUA1:55 pmOranjestad Reina Beatrix
Dec 22
AUA4:35 pmOranjestad Reina Beatrix
22h 19m
2 stops
ORD12:54 pmChicago O'Hare Intl
$358
Find similar

American Airlines flights from Wisconsin to Caribbean Islands

Our best American Airlines deals on Wisconsin to Caribbean Islands flight tickets
American Airlines
Jan 18
ORD3:15 pmChicago O'Hare Intl
4h 39m
SJU9:54 pmSan Juan Luis Munoz Marin Intl
Jan 29
SJU4:28 pmSan Juan Luis Munoz Marin Intl
5h 32m
ORD8:00 pmChicago O'Hare Intl
$243
Find similar
American Airlines
Feb 4
ORD8:45 amChicago O'Hare Intl
5h 05m
AUA3:50 pmOranjestad Reina Beatrix
Feb 9
AUA5:59 pmOranjestad Reina Beatrix
17h 06m
1 stop
ORD9:05 amChicago O'Hare Intl
$353
Find similar
American Airlines
Dec 4
ORD2:40 pmChicago O'Hare Intl
22h 02m
1 stop
AUA2:42 pmOranjestad Reina Beatrix
Dec 9
AUA5:59 pmOranjestad Reina Beatrix
16h 50m
1 stop
ORD8:49 amChicago O'Hare Intl
$355
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Wisconsin to Caribbean Islands that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated November 5, 2025.
Use the filters below to find and compare flights from Wisconsin to Caribbean Islands that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 12/10

3:26 pm-12:32 pm

1 stop19h 06m

San Juan Luis Munoz Marin Intl

Sun 12/14

1:59 am-2:03 pm

1 stop14h 04m

$210

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 12/10

12:09 pm-12:16 am

1 stop10h 07m

San Juan Luis Munoz Marin Intl

Sun 12/14

1:59 am-2:03 pm

1 stop14h 04m

$211

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 11/24

11:40 am-9:50 pm

1 stop8h 10m

San Juan Luis Munoz Marin Intl

Fri 12/5

8:45 pm-11:59 pm

Nonstop5h 14m

$215

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 1/10

6:11 pm-10:17 am

1 stop14h 06m

San Juan Luis Munoz Marin Intl

Sat 1/17

2:29 am-2:13 pm

1 stop13h 44m

$216

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 12/3

8:41 am-3:17 pm

Nonstop4h 36m

San Juan Luis Munoz Marin Intl

Mon 12/15

8:45 pm-11:59 pm

Nonstop5h 14m

$217

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 1/19

2:20 pm-9:00 pm

Nonstop4h 40m

San Juan Luis Munoz Marin Intl

Fri 1/23

4:52 pm-8:20 pm

Nonstop5h 28m

$218

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 1/18

7:51 pm-4:55 pm

2 stops19h 04m

San Juan Luis Munoz Marin Intl

Fri 1/30

4:11 pm-11:35 pm

1 stop9h 24m

$220

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 1/19

11:18 am-11:44 pm

1 stop10h 26m

San Juan Luis Munoz Marin Intl

Tue 1/27

6:27 pm-11:57 pm

1 stop7h 30m

$227

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Mon 12/8

6:00 am-5:25 pm

1 stop9h 25m

Punta Cana

Mon 12/15

2:55 pm-6:08 pm

Nonstop5h 13m

$293

ChicagoPunta Cana

ORD - PUJ

ORDPUJ

Chicago O'Hare Intl

Sun 1/25

5:20 pm-1:30 pm

1 stop18h 10m

Punta Cana

Thu 2/5

2:32 pm-9:42 pm

1 stop9h 10m

$342

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

See travel insights to Caribbean Islands from

How to get the cheapest flight ticket from Wisconsin to Caribbean Islands

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Caribbean Islands?

The month of September is, on average, the cheapest month to fly to Caribbean Islands from Wisconsin, with most prices found around $315. The month of October is another great option to travel to Caribbean Islands, with average flight prices from Wisconsin averaging around $338.

What is the cheapest day to depart on your flight to Caribbean Islands?

The cheapest day to depart from Wisconsin to Caribbean Islands is on a Tuesday. Travelers who choose to depart for Caribbean Islands on a Tuesday will often find tickets for as low as $389. If your travel schedule is flexible, try to avoid departing on a Friday because tickets tend to average around $477. These prices are subject to change though, so be sure to set up a Price Alert for flights to Caribbean Islands.

What is the cheapest time of day to depart on your flight to Caribbean Islands?

According to our data, the cheapest time of day to fly to Caribbean Islands is in the evening. momondo users have found flights departing from Wisconsin to Caribbean Islands in the evening for as low as $360. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. Try not to purchase tickets at noon because they tend to be around $458. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Wisconsin to Caribbean Islands flight route?

Fly from Milwaukee-Mitchell to Montego Bay Sangster Intl for the best Wisconsin - Caribbean Islands flight prices

How far in advance should I book a flight to Caribbean Islands?

You are more likely to see cheaper flights to Caribbean Islands from Wisconsin when booking weeks ahead of your departure date. In general, you can expect to find flights to Caribbean Islands for around $436 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Caribbean Islands from Wisconsin for as low as $299 on momondo.

What cabin class options are available on Wisconsin to Caribbean Islands flights?

There is only 1 cabin class available to choose from on Wisconsin to Caribbean Islands flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Wisconsin to Caribbean Islands flights?

No. A direct flight is the cheapest option for a flight between Wisconsin to Caribbean Islands.

Cheap Wisconsin to Caribbean Islands flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Wisconsin to Caribbean Islands

Fastest flight time

3h 18m

Direct flights

Every day

Airports in Caribbean Islands

3 airports
The fastest flight from Wisconsin to Caribbean Islands takes 3h 18m
Direct flights go from Wisconsin to Caribbean Islands every day.
There are 3 airports near Caribbean Islands: Nassau Intl (NAS), Montego Bay Sangster Intl (MBJ), Providenciales (PLS)
Search flight deals

  • When did momondo last update prices for flights from Wisconsin to Caribbean Islands?

    Prices for flights from Wisconsin to Caribbean Islands refresh daily.

  • How many operators does momondo search for flights from Wisconsin to Caribbean Islands?

  • How old do you have to be to fly from Wisconsin to Caribbean Islands?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Wisconsin to Caribbean Islands.

  • What documentation or ID do you need to fly to Caribbean Islands?

    The required travel and health documents for your Caribbean Islands trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Caribbean Islands. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular plane model from Wisconsin to Caribbean Islands?

Best airlines flying from Wisconsin to Caribbean Islands

Compare and see reviews for airlines that fly from Wisconsin to Caribbean Islands with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $129Free CancellationRating
5.8
3,115 reviews
Search Frontier flights
United AirlinesPriceFrom $202Free CancellationRating
7.4
9,000 reviews
Search United Airlines flights
DeltaPriceFrom $215Free CancellationRating
7.9
8,004 reviews
Search Delta flights
Spirit AirlinesPriceFrom $226Free CancellationRating
6.3
8,113 reviews
Search Spirit Airlines flights
American AirlinesPriceFrom $269Free CancellationRating
7.2
11,041 reviews
Search American Airlines flights
SouthwestPriceFrom $315Free CancellationRating
8.0
4,239 reviews
Search Southwest flights
Sun Country AirPriceFrom $540Free CancellationRating
6.9
335 reviews
Search Sun Country Air flights

Why use momondo?

Why should I use momondo to find a flight deal from Wisconsin to Caribbean Islands?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Wisconsin to Caribbean Islands. momondo saves you time and could save you money on your trip.

Can I find flights from Wisconsin to Caribbean Islands with flexible booking policies on momondo?

Yes. All flights to Caribbean Islands from Wisconsin on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Wisconsin to Caribbean Islands?

momondo provides multiple filters to help you find the best flight to Caribbean Islands from Wisconsin. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Wisconsin to Caribbean Islands right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Wisconsin to Caribbean Islands now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Caribbean Islands and let you know when they change.

An easier way to manage your Caribbean Islands trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Fri 12/5
Fri 12/12
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Caribbean Islands

Popular cities in Caribbean Islands

Popular flights according to clicks in the last 7 days on momondo
Flights to New Yorkfrom $44
Flights to Londonfrom $320
Flights to Bangkokfrom $507
Flights to Tokyofrom $381
Flights to Los Angelesfrom $49
Flights to Parisfrom $340
Flights to Copenhagenfrom $358
Flights to Istanbulfrom $373
Flights to Manilafrom $521
Flights to Romefrom $321
Flights to Miamifrom $49
Flights to Chicagofrom $54